“There is nothing more deceptive than an obvious fact.” —Arthur Conan Doyle
Leadership is often associated with vision, strategy and decision-making. But one of the most overlooked dangers I’ve seen in my work with executives has less to do with what leaders do and more to do with what they assume.
As author Don Miguel Ruiz reminds us in The Four Agreements, the third agreement is: Don’t make assumptions. Simple in principle, hard in practice.
We carry our assumptions, knowledge and context into every conversation. Our words make perfect sense to us. But for others — who lack our access to data, backroom discussions or historical perspective — there’s often a lot of room for misinterpretation. The result? Nods around the table feel like agreement. But they often aren’t.
At the heart of this problem is a concept introduced by philosopher and entrepreneur Fernando Flores: the background of obviousness. While the term sounds philosophical, its implications for leadership are deeply practical. It refers to the invisible context we bring to every interaction — the assumptions and understandings we’ve internalized through experience and culture.
What’s more, the higher we climb in leadership, the more our background of obviousness diverges from that of our team.
Consider a leader who says, “We need to move faster.” That simple phrase may carry a mountain of unspoken meaning: falling behind competitors, boardroom pressure or looming investor scrutiny. But to the team, it might simply sound like a request to tighten a project timeline.
This kind of disconnect is subtle but powerful. Like a cognitive bias, it’s often invisible until it causes a breakdown. As Daniel Kahneman noted in Thinking, Fast and Slow, our fast-thinking brains rely heavily on assumptions and intuition. In leadership, those assumptions often go unexamined — until it’s too late.
In Understanding Computers and Cognition, Flores and computer scientist Terry Winograd challenged the idea that communication is simply about transmitting facts. Language, they argued, isn’t a neutral tool. It’s shaped by history, identity and interaction. Communication is less like delivering a message and more like playing jazz — it depends on rhythm, cues, and most crucially, a shared background of obviousness.
A hidden leadership blind spot
Access is one of the perks of leadership — access to information, high-level conversations, strategic direction. But that privilege becomes a liability when we forget that others aren’t working with the same inputs.
This isn’t about ego. It’s simply human nature. We all assume others share our perspective. But leaders are especially prone to this trap because their words carry disproportionate weight. What may seem like a casual suggestion to you can sound like a directive to your team.
Here’s how the trap can show up:
- A CEO shares a “simple strategy,” unaware that the team lacks the financial literacy to grasp its implications.
- A manager sets a goal without explaining what “success” looks like, assuming everyone shares the same standard.
- A project falters because no one asks for clarification — no one wants to admit they don’t understand what the leader meant.
The issue isn’t that the leader is wrong. It’s that their internal map — the one guiding their decisions — is invisible to others.
Examples in action
I once worked with an executive who was frustrated that her team “wasn’t thinking big enough.” As we dug deeper, it became clear she had just come from weeks of strategic meetings with the board. Her team, meanwhile, was focused on client needs and quarterly deliverables. Her call for “bold moves” didn’t land — not because the team lacked ambition, but because they lacked the context behind her request.
In another case, a startup founder told his engineers to “optimize the user journey.” For him, that meant a complete overhaul of the onboarding experience. For them, it meant improving load times. After weeks of misaligned work, both sides were disappointed. Each side had operated in good faith, but from different assumptions.
And on a lighter note: I once told my kids I’d pay them five dollars each to rake the leaves. I returned to find a few big piles, scattered leaves still blanketing the yard and two eager faces asking for their cash. What “raking the leaves” meant to me was far from what it meant to them — cue disappointment on all sides.
Making the invisible visible
As a leader, you can avoid this trap by employing these strategies:
- Slow down your declarations. Before giving directives, pause. Ask: What do I know that others might not? What assumptions am I making?
- Check for shared meaning. Ask team members what a term or objective means to them. If the answers differ, you’ve uncovered a gap worth discussing.
- Invite clarification. Encourage others to speak up when something doesn’t make sense. Create safety around questions and alternative perspectives.
- Narrate your thinking. Don’t just share the what of your position. Let people in on the thought process behind your decisions. Share the why, how and for whom it matters.
These aren’t just communication techniques — they’re acts of leadership humility. They acknowledge that others don’t inhabit your worldview. And that’s not a flaw; it’s a strength.
Why it matters
Today’s leaders are under enormous pressure to move fast, inspire teams and deliver results in complex, high-stakes environments. But if we skip the work of building shared understanding, we end up with fragile alignment: people appear to agree — until execution reveals they don’t.
You can’t eliminate the background of obviousness but it can be brought to the surface. And when it is, leaders gain more clarity, more engagement and better outcomes.
Flores captured it best: “Transformation begins when we become aware of what has been concealed by its obviousness.”
Opinions expressed by SmartBrief contributors are their own.
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